{{Short description|Chemical compound}} {{Infobox drug | Watchedfields = changed | verifiedrevid = 412749783 | type = <!-- empty --> | image = Diethylcarbamazine.svg | image_class = skin-invert-image | width = | alt = | caption = | image2 = Diethylcarbamazine ball-and-stick model from xtal 2010.png | image_class2 = bg-transparent | width2 = 250px
<!-- Clinical data --> | pronounce = | tradename= | Drugs.com = {{drugs.com|CONS|diethylcarbamazine}} | MedlinePlus = | DailyMedID = <!-- DailyMed may use generic or brand name (generic name preferred) --> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU_comment = | pregnancy_category = | routes_of_administration = By mouth | class = | ATCvet = | ATC_prefix = P02 | ATC_suffix = CB02 | ATC_supplemental = {{ATCvet|P52|AH02}}
<!-- Legal status --> | legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled --> | legal_AU_comment = | legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F --> | legal_BR_comment = | legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_CA_comment = | legal_DE = <!-- Anlage I, II, III or Unscheduled --> | legal_DE_comment = | legal_NZ = <!-- Class A, B, C --> | legal_NZ_comment = | legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C --> | legal_UK_comment = | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_US_comment = | legal_EU = | legal_EU_comment = | legal_UN = <!-- N I, II, III, IV / P I, II, III, IV --> | legal_UN_comment = | legal_status = Rx Only
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = | excretion =
<!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 90-89-1 | CAS_supplemental = | PubChem = 3052 | IUPHAR_ligand = | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB00711 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 2944 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = V867Q8X3ZD | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D07825 | ChEBI = | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 684 | NIAID_ChemDB = | PDB_ligand = | synonyms= DEC, ''N'', ''N''-diethyl-4-methyl-1-piperazine carboxamide
<!-- Chemical and physical data --> | IUPAC_name = ''N,N''-diethyl-4-methylpiperazine-1-carboxamide | C=10 | H=21 | N=3 | O=1 | SMILES = C1CN(C)CCN1C(=O)N(CC)CC | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C10H21N3O/c1-4-12(5-2)10(14)13-8-6-11(3)7-9-13/h4-9H2,1-3H3 | StdInChI_comment = | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = RCKMWOKWVGPNJF-UHFFFAOYSA-N | density = | density_notes = | melting_point = 47 | melting_high = 49 | melting_notes = | boiling_point = | boiling_notes = | solubility = | sol_units = | specific_rotation = }}
<!-- Definition and medical uses --> '''Diethylcarbamazine''' is a medication used in the treatment of filariasis including lymphatic filariasis, tropical pulmonary eosinophilia, and loiasis.<ref name=CDC2016/> It may also be used for prevention of loiasis in those at high risk.<ref name=CDC2016>{{cite web|title=Our Formulary Infectious Diseases Laboratories CDC|url=https://www.cdc.gov/laboratory/drugservice/formulary.html|website=www.cdc.gov|access-date=7 December 2016|date=22 September 2016|url-status=live|archive-url=https://web.archive.org/web/20161216173833/https://www.cdc.gov/laboratory/drugservice/formulary.html|archive-date=16 December 2016}}</ref> While it has been used for onchocerciasis (river blindness), ivermectin is preferred.<ref name=WHO2008/> It is taken by mouth.<ref name=Drug2016/>
<!-- Side effects and mechanism --> Common side effects include itching, facial swelling, headaches, and feeling tired.<ref name=Drug2016/> Other side effects include vision loss and dizziness.<ref name=Drug2016>{{cite web|title=Diethylcarbamazine Advanced Patient Information - Drugs.com|url=https://www.drugs.com/cons/diethylcarbamazine.html|website=www.drugs.com|access-date=8 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161220223430/https://www.drugs.com/cons/diethylcarbamazine.html|archive-date=20 December 2016}}</ref> It is a recommended treatment in pregnancy and appears to be safe for the baby.<ref>{{cite book| vauthors = Sweet RL, Gibbs RS |title=Infectious Diseases of the Female Genital Tract|date=2009|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-7815-2|page=382|url=https://books.google.com/books?id=wuR_ngItU5oC&pg=PA382|language=en|url-status=live|archive-url=https://web.archive.org/web/20170910145628/https://books.google.com/books?id=wuR_ngItU5oC&pg=PA382|archive-date=2017-09-10}}</ref><ref>{{cite book| vauthors = Herbert-Ashton M, Clarkson NE |title=Quick Look Nursing: Pharmacology|date=2005|publisher=Jones & Bartlett Learning|isbn=978-0-7637-3595-1|page=48|url=https://books.google.com/books?id=RuyTlze9Y5kC&pg=PA48|language=en|url-status=live|archive-url=https://web.archive.org/web/20170910145628/https://books.google.com/books?id=RuyTlze9Y5kC&pg=PA48|archive-date=2017-09-10}}</ref> The World Health Organization; however, recommends waiting until after pregnancy for treatment when feasible.<ref name=WHO2008>{{cite book | title = WHO Model Formulary 2008 | year = 2009 | isbn = 978-92-4-154765-9 | veditors = Stuart MC, Kouimtzi M, Hill SR | hdl = 10665/44053 | publisher = World Health Organization | hdl-access=free |page=91 }}</ref> It is made from 4-methyl-piperazine.<ref>{{cite web|title=WHO Model Prescribing Information: Drugs Used in Parasitic Diseases - Second Edition: Helminths: Lymphatic filariasis: Diethylcarbamazine|url=http://apps.who.int/medicinedocs/en/d/Jh2922e/3.5.1.html|website=apps.who.int|access-date=8 December 2016|page=152|date=1995|archive-url=https://web.archive.org/web/20161120192136/http://apps.who.int/medicinedocs/en/d/Jh2922e/3.5.1.html|archive-date=20 November 2016}}</ref>
<!-- History and culture --> Diethylcarbamazine was discovered in 1947<ref>{{cite book| vauthors = Busvine J |title=Disease Transmission by Insects: Its Discovery and 90 Years of Effort to Prevent it|date=2012|publisher=Springer Science & Business Media|isbn=978-3-642-45716-6|page=260|url=https://books.google.com/books?id=POnvCAAAQBAJ&pg=PA260|language=en|url-status=live|archive-url=https://web.archive.org/web/20170910145628/https://books.google.com/books?id=POnvCAAAQBAJ&pg=PA260|archive-date=2017-09-10}}</ref> by Yellapragada Subbarow.<ref name="Hewitt-et-al-1948">{{cite journal | vauthors = Hewitt R, Wallace W | title = The treatment of ascariasis in dogs with 1-diethylcarbamyl-4-methylpiperazine hydrochloride | journal = The Journal of Parasitology | volume = 34 | issue = 3 | pages = 237–239 | date = June 1948 | pmid = 18867399 | doi = 10.2307/3273270 | s2cid = 43592055 | jstor = 3273270 }}</ref><ref>{{cite journal| vauthors = Kamath P, Shenoy KA |date=2013|title=Yellapragada Subba Rao: The Unsung Hero|url=https://www.mjmsr.net/article.asp?issn=0975-9727;year=2013;volume=4;issue=2;spage=130;epage=132;aulast=Kamath|journal=Muller Journal of Medical Sciences and Research|volume=4|issue=2|pages=130–132|doi=10.4103/0975-9727.118248|s2cid=72843672|doi-access=free}}</ref> It is on the World Health Organization's List of Essential Medicines.<ref name="WHO21st">{{cite book | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref> It is not commercially available in the United States but can be acquired from the Centers for Disease Control and Prevention.<ref name=CDC2016/>
==Medical uses== Diethylcarbamazine is indicated for the treatment of people with certain filarial diseases, including lymphatic filariasis caused by infection with ''Wuchereria bancrofti'', ''Brugia malayi'', or ''Brugia timori''; loiasis and tropical pulmonary eosinophilia.<ref name="Ottesen 1985 pp. 341–356">{{cite journal | vauthors = Ottesen EA | title = Efficacy of diethylcarbamazine in eradicating infection with lymphatic-dwelling filariae in humans | journal = Reviews of Infectious Diseases | volume = 7 | issue = 3 | pages = 341–356 | year = 1985 | pmid = 3895352 | doi = 10.1093/clinids/7.3.341 | publisher = Oxford University Press | jstor = 4453627 }}</ref> The WHO recommends prescribing diethylcarbamazine to people who are infected with microfilariae of filarial parasites and also to control transmission of infection in filariasis-endemic areas.{{citation needed|date=May 2021}}
In India and China, diethylcarbamazine has been added to salt to combat lymphatic filariasis.<ref name="Lammie_2007">{{cite journal | vauthors = Lammie P, Milner T, Houston R | title = Unfulfilled potential: using diethylcarbamazine-fortified salt to eliminate lymphatic filariasis | journal = Bulletin of the World Health Organization | volume = 85 | issue = 7 | pages = 545–549 | date = July 2007 | pmid = 17768503 | pmc = 2636360 | doi = 10.2471/blt.06.034108 }}</ref>
== Contraindications == Contraindications are previous history of heart problems, gastrointestinal problems, and allergies.{{medical citation needed|date=September 2015}}
Diethylcarbamazine is contraindicated in patients who may have onchocerciasis, due to the risk of the Mazzotti reaction.<ref>{{Cite web |date=2020-10-26 |title=Lymphatic Filariasis - Resources for Health Professionals - Guidance for Evaluation and Treatment |url=https://www.cdc.gov/parasites/lymphaticfilariasis/health_professionals/dxtx.html |access-date=2022-05-06 |website=U.S. Centers for Disease Control and Prevention (CDC) }}</ref>
==Mechanism== Diethylcarbamazine is an inhibitor of arachidonic acid metabolism in microfilariae. This makes the microfilariae more susceptible to innate immune attack, but does not kill the parasites outright.<ref>{{cite journal | vauthors = El-Shahawi GA, Abdel-Latif M, Saad AH, Bahgat M | title = Setaria equina: in vivo effect of diethylcarbamazine citrate on microfilariae in albino rats | journal = Experimental Parasitology | volume = 126 | issue = 4 | pages = 603–610 | date = December 2010 | pmid = 20599991 | doi = 10.1016/j.exppara.2010.06.022 }}</ref>
== Society and culture == === Brand names === Brand names include Hetrazan, Carbilazine, Caricide, Cypip, Ethodryl, Notézine, Spatonin, Filaribits, Banocide Forte, and Eofil.{{citation needed|date=September 2022}}
== Veterinary uses ==
Diethylcarbamazine is used to prevent heartworm in dogs.{{citation needed|date=May 2021}}
== References == {{reflist}}
== External links == * {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/diethylcarbamazine | archive-url = https://web.archive.org/web/20200715152907/https://druginfo.nlm.nih.gov/drugportal/name/diethylcarbamazine | archive-date = July 15, 2020 | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Diethylcarbamazine }}
{{Anthelmintics}} {{Piperazines}} {{Portal bar|Medicine}}
Category:Antiparasitic agents Category:Lymphatic filariasis Category:4-Methylpiperazin-1-yl compounds Category:Ureas Category:Wikipedia medicine articles ready to translate Category:World Health Organization essential medicines